What’s it like to be with a Trans Women Sex Worker?

Guest Blog: Lingerie Boy & his experiences with Trans Women Sex Workers

As a preface would just like to emphasise, for avoidance of doubt, that this article is written as an experiential and observational piece; regarding my encounters with Trans Sex Workers (TSW) who form the bulk of my experiences with Trans Women (TW).

Many have become friends and I have been fortunate to meet several extremely courageous and beautiful women, all of whom have had to fight terrible prejudice and abuse.

Does visiting a TSW make you gay?

Absolutely not, nothing makes you gay unless you are born with that orientation!

From my experience the vast majority of men and women who are attracted to TW are straight or bi. In my case happen to be a straight man who likes to dress in lingerie and feminine attire in sexual situations, a Sissy in the main. 

As a Sissy guy always attracted to women, I developed a need to express this sexually with another person as I reached adulthood and my 20’s. From bitter experience sharing my desire to dress up with girlfriends and casual acquaintances was humiliating, thus decided to restrict my overt Sissy sexual activity with Sex Workers who are by definition far less narrow minded and judgemental.

This was fabulous I could relax and feel sexually accepted, plus hugely satisfying, solved my erotic needs and frankly a wonderfully exciting revelation! As is often the way soon became interested in being a more passive partner in these liaisons, starting with toys soon progressed to being pegged.

This was doubly exciting! As with many Sissies playing the part of a woman in a quasi-lesbian way is the ultimate fantasy. I would add that for me being the passive person didn’t mean being dominated in a forceful way, light spanking and of course pleasing my partner sexually. On occasion we would also have intercourse, something that became less prevalent as my journey evolved.

With the rise of internet pornography there was of course an explosion of content covering all sorts of genres. An early star for me was Strapon Jane who produced a huge amount of content, much of which involved pegging transformed Sissies – www.straponjane.com. Nirvana had arrived! 

Curiosity naturally meant that I began to think would being f*cked by a real cock be the ultimate exposition of my Sissy fantasies. As a straight guy this meant not looking at male porn but Transexual porn. A huge amount of which dealt with active TW f*cking guys, this became increasingly irresistible, not least having discovered a Brazilian site shemalesissification.com. No longer working I’m afraid, the content involved completely sissifying men and then f*cking them, even greater Nirvana!

I can resist anything except temptation, so I felt increasingly drawn to explore my new fantasy!

What attracts you to Trans Women?

As above the initial attraction was largely the opportunity to engage a TSW to Sissify me and have her wicked way. At a non-sexual level am also attracted to women, so inevitably find many TW sexy!

The opportunity to be the passive party in a sexual liaison where the dominant party was willing to play an active role with her cock was by this point irresistible. So, I of course took the plunge and was fortunate to meet many TSW, several of whom became friends over time which was fabulous. It was flattering indeed to be invited to dinner etc. on a friend basis by a couple of amazing TW.

I would add that this has been very much the exception, in the main my liaisons have remained on a professional/transactional basis only.

How to find a TSW?

I have visited a number of sites dealing with TSW. A few below:-




In conjunction, I also sought out reviews, as with any professional service it is wise to do so. Depending on what you are looking for the reviews do give an insight into personality, attitude etc. https://www.shemalewiki.com/

Having had some very disappointing experiences every now and then would recommend seeking reviews before visiting a TSW. Most are great, but occasionally as with anything not so great!

What are your experiences with TSW?

Trans women sex worker
Guest blog – Lingerie boy

How long have you got? Over the years have had predominantly wonderful experiences and as above a few friendships outside of the pure transactional arena. There are many Latin American TSW in the UK, often very sexy, but language can be a bit of a barrier so worth establishing that beforehand. But even so, with google translate etc. it doesn’t take long to establish what you are looking for!

I have had some incredible sexual experiences with TSW, more recently been involved in producing content for Onlyfans and other platforms so can definitely say my experiences have covered pretty much every fantasy and more 😉

The most important thing is to treat TSW with respect, be clean, be clear about your motivations, plus don’t try negotiating discounts. AND never waste their time, it’s incredibly rude and disrespectful, don’t forget all SW are running a business and not there for you to take the piss!

Red flags in the TSW community

  • Treat all TW with respect, if you are Transphobic stay away – For me that is the big red flag of course. 
  • That apart be clear what you want, be honest, be respectful and don’t expect more than you’ve agreed. 

Tips for building and maintaining long term relationships with TSW

  • As with any relationships it is all about being truthful, respectful etc. as above.
  • That said, remember that you are involved in engaging with a TSW, not in a romantic sense, if friendship or more develops so be it. 
  • Don’t entertain greater aspirations, even when you know someone well unless she makes it very clear that perhaps something closer is feasible.
  • If you are looking for love and a LTR go to dating sites!

Lingerie Boy 

There we have it, Kinksters! 

I hope you enjoyed reading this guest blog. A massive shout-out to Satin Lingerie Boy!

>>>Click here to follow Satin Lingerie Boy on Twitter or on OnlyFans so you don’t miss the latest

Have you ever been with a trans women sex worker? Ever thought about?! Do you know someone who might be? Let’s support each other, Kinksters! So please feel free to SHARE this interview blog with others. Feel free to hit me up on Twitter @podofeleus and Instagram @Podopheleus, or my contact page.

Much Kink Love,



P.S. if you’re interested to find out more about being a sissy and stories involving this fetish – read some of my other blogs on this topic here!

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